When I was just a child in school,I asked my teacher, “What will I try?”Should I paint pictures, should I sing songs?”This was her wise reply: “Que sera, sera. Whatever will be, will be.The future’s not ours to see. Que sera, sera.”

These days, many boomers are having their own Que Sera Sera moment, wondering “what they will try” next and whether they can afford to do it in “unretirement.” Start a company? Continue working full-time, maybe at a different company or industry? Shift to part-time or contract work?

Many want to keep earning an income — from something that’s meaningful. In other words, doing well personally and doing good socially.

But, as Harvard University psychology professor and Stumbling on Happiness author Daniel Gilbert observes, the Que Sera Sera teacher’s reply isn’t that wise or helpful. Instead, he recommends exploring your possibilities by learning from surrogates: people engaged in something that attracts you.

“Teachers, neighbors, coworkers, parents, friends, lovers, children, uncles, cousins, coaches, cabdrivers, bartenders, hairstylists, dentists, advertisers — each of these folks has something to say about what it would be like to live in this future rather than that one, and at any point in time we can be fairly sure that one of these folks has actually had the experience that we are merely contemplating,” Gilbert writes in Stumbling on Happiness.

Then, if you determine that your next move will mean an income cut, I believe you should start getting more frugal, so you can enjoy your new life without feeling squeezed.

Wise Words From A Transition Pro

To learn more about major midlife transitions, I reached out to Harlan Limpert, the 64-year-old Chief Operating Officer for the Unitarian Universalist Association, the church group’s umbrella organization, and former head of human resources at Target.

Due to his career path, many people have informally consulted with Limpert over the years for advice about finding meaning and purpose through work (full-time or part-time).

Limpert worked in HR for two years at Target in Minneapolis after college in the early 1970s. It was a good job, he says, but he felt it didn’t offer enough in terms of life’s meaning. So he went to seminary at Starr King School for the Ministry for Unitarian Universalists in Berkeley, Calif. and then became a chaplain at St. Elizabeth’s, the mental hospital in Washington, D.C.

Although he found chaplaincy rewarding, Limpert felt it wasn’t the right career for him and, after two years, headed back to Target. While at Target, Limpert stayed engaged with a local congregation. And in 2001, at 51, he quit the HR job to become the Unitarian Universalist Association’s director of lay leadership development — a shift that took advantage of his human resource skills but also came with a significant cut in pay.

These days, Limpert spends three weeks a month at its headquarters in Boston and one week back home in Minneapolis. “It’s the perfect job for me,” he says.

Limpert's 2 Rules to Follow

In a wide-ranging conversation, Limpert stressed two points for anyone thinking through a major transition:

First, investigate carefully any potential job or career options before leaping into a new endeavor. “The romanticism of the ‘other’ is a huge mistake people make,” he cautions.

In particular, if you’ve labored in the private sector, don’t put on rose-colored glasses about jobs in the nonprofit world. “People think business is hard and bad and the nonprofit world is good and easy,” he says. “Well, no. The question to pursue is, ‘How can I get a realistic picture of what my next life might be?’”

Do your research. Get involved. And, as Gilbert emphasized and Limpert reinforced, talk to lots of people engaged in the kind of job you believe will give you greater emotional and mental satisfaction and financial security.

Limpert’s second major point: A frugal lifestyle will help you fund and succeed at a major transition.

Many unretirement jobs come with a reduced salary; it’s a typical trade-off for the greater flexibility that comes with part-time or contract work. And full-time employees often take a hit if they move from the for-profit sector to the nonprofit world.

The career switch was financially easy for Limpert because he and his wife have always lived relatively modestly, focusing their spending on their children’s education and travel rather than on a big house or luxury cars. By living frugally, “you’re in a position to accept a reduced income,” says Limpert. “You have the economic flexibility to do what you want.”

Frugality Isn't Pennypinching

Of course, mention frugality or thrift and words like stingy, cheap and hoarding quickly some to mind. Big mistake.

David Starr Jordan, the founding president of Stanford University, rightly noted in a 1915 talk that thrift “does not involve stinginess, which is an abuse of thrift, nor does it require that each item of savings should be financial investments; the money that is spent on the education of one’s self or of one’s family, in travel, in music, in art, or in helpfulness to others, if it brings real returns in personal development or in a better understanding of the world we live in, is in accordance with the spirit of thrift.”

In today’s world, many of my fellow boomers know they wrongly equated the good life with owning lots of stuff. In our hearts, we’ve always known that what gives us genuine satisfaction are experiences and creativity; family and community; a sense of purpose and a spirit of generosity.

Thrift is essentially a mindset for trying to match your spending with your values. “Cheapskates aim to buy as much as they can for as little as possible, not caring much for the quality or environmental or ethical virtues of the items they’re consuming,” Farhad Manjoo wrote when he was Slate’s technology columnist. “To be frugal, on the other hand, is to consider the full ramifications of every purchase.”

Okay, what if you’ve been more spendthrift than thrifty? In that case, work on creating a more frugal lifestyle into your unretirement planning while you’re investigating options for meaningful work.

How to Become More Frugal

The two efforts go hand in hand. There is no shortage of resources for practical suggestions.

Websites like The Simple Dollar and comprehensive, free or low-cost online financial calculators such as those at Analyzenow.com offer the kind of frugal information that can help turn the dream of an encore job into a financially-realistic pursuit.

Simply put, the payoff from pursuing conversations with job surrogates and adopting a frugal approach to money in your unretirement planning is potentially huge — financially and emotionally.

Chris Farrell is writing about Unretirement twice a month, focusing on the personal finance and entrepreneurial start-up implications and the lessons people learn as they search for meaning and income. Tell him about your experiences so he can address your questions in future columns. Send your queries to him at [email protected]. His twitter address is @cfarrellecon.